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scp checks existence in the wrong orderscp's primary purpose is not to validate the existence of files, but rather secure file transfer, so it makes sense that it prioritizes making a secure connection, before file operations. I would recommend reading the RFC for SSH for a fuller understanding of the technical details of the protocol and it's reasons for working as it does.

ssh without using the user's default shellWhen you say you tried writing a custom subsystem, it sounds like you configured one in sshd_config, but didn't actually write the necessary source code within a custom sshd binary to support it, correct? My hazy recollection from working on a project forked from OpenSSH is that actual coding and recompling is required, not just configuration.

Cannot enter Sudo password when controlling Linux Mint with SynergyHave you tried opening a simple text editor on the Mint box, and seeing if you can enter your password there without issue? Some special characters might not be making it through, and it would be the easiest way to tell if the password is getting sent correctly or not....